*This is part two of the previous [post](https://www.reddit.com/r/eroticliterature/comments/z34mn9/advanced_blowjob_howto_mf_oral_deepthroat_18_pt1/?utm_source=share&utm_medium=ios_app&utm_name=iossmf) I made. Apparently I wrote too much for one post. Please read that post and disclaimer before this one. Enjoy!*
Another fun variation of a blowjob is to play with his ass while you do it. This is a super important one that you ask before doing it. You can feel it out by massaging his taint (the space between his balls and asshole) while sucking his dick, but before you go lower get verbal consent. While you’re playing with his balls move lower and brush his taint with your fingers. Slowly increase the pressure until you’re GENTLY but firmly rubbing that area. You can move in circles or back and forth. Try different areas to see which parts of it are most sensitive for him. Now is when you ask if you can go lower IF he’s responding positively. If he doesn’t seem into it I’d stop touching the taint and ask him after sex if that’s something he’d like to try again in the future.
Make sure your fingers are wet with spit (or lube) and that he’s showered recently and clean. I usually address hygiene early on in a relationship but better late than never. It’s best if he goes up to one knuckle deep in the shower with his fingers to make sure the entrance is clean. If you’re going to be penetrating him it’s best to do this after he’s had a good, clean bowel movement. For anal fingering I don’t find anything more than that is necessary. Yes you may find some poop. Totally normal and it doesn’t bother me at all. If you are going to be fingering him I’d make sure it’s close to the end of the blowjob so you don’t have to pull your fingers out halfway through because the first thing you would do after that is definitely wash your hands. You can wear gloves if you want, but make sure you use lube! And don’t rim him after you’ve fingered him, that’s just asking for trouble.
Now that the logistics are out of the way, slowly circle his asshole with your finger. Keep the pressure very light. Spit on your fingers to make sure he stays wet. To help you he should spread his legs and put his knees up so you have better access. Continue sucking his dick and using your hands to stroke his shaft. If he’s responding favorably you can move to rimming. Really get in there. Keep jerking him off with your hand (remember to keep it nice and wet with spit) and start licking his asshole. Start with teasing strokes and then ramp up to really eating his ass. Get as much in there as you can, show your enthusiasm. Moan while you lick him, pull back and compliment his ass. When your jaw gets tired keep teasing his asshole with your fingers.
The next part needs a conversation ahead of time. I don’t recommend penetrating anyone without ENTHUSIASTIC consent. But if you’ve determined it’s something you’d both like to try, get some lube, slather it all over his hole and your fingers, and slowly insert one finger inside of him. I wouldn’t recommend moving your finger in and out of any asshole as it feels weird (like you’re pooping). Instead slide it in slowly, stopping to let him get used to it, and then curl your finger upward once you’re inside. Feel for a walnut shaped hard spot inside. This is the prostate, or p-spot. The next part really depends on the guys preferences. Try stroking it directly and asking if that’s okay. He may prefer indirect touch, either in front, behind, or to the side. Try different pressures. Try moving your fingers in circles or rubbing forward and backward. Whatever you do, be as gentle as possible. Only go harder if he asks for it. Right now you’re just exploring, you can always go harder next time.
Keep in constant communication with him while you’re fingering him. “Do you like that?” “Do you want me to go softer/harder?” Do you prefer this or that?” Until you’ve established what he likes. Usually you can feel if he’s loosened enough for another finger. If he’s tight like a vice don’t even ask, if he’s relaxed a bit ask if he wants another finger. Use more lube!! Keep stroking his dick while you’re doing all this.
Once you’ve determined a good speed/pressure he likes, go back to sucking his dick. Keep it simple with an up/down motion, use your hand to help out your mouth, and maybe add a little twist every time you reach the top of the stroke. By now you should know his finishing move. Is it hearing you moan? Is it sucking harder to apply pressure? Is it flicking the underside of his head with your tongue? Is it twisting your wrist as you go up and down? Is it moving the skin up over the head of his cock on every stroke? Is it gliding gently over his head and lifting off with your mouth every time to get that delicious “pop” noise? Do whatever is his favorite, and I’m sure in no time at all he’ll be cumming.
Also be sure you know what his favorite thing for you to do is while he cums. I’ve found a good place to start is to slightly ease off with the pressure and stay away from the head while he comes. Move your hand slowly but firmly to milk out the last drops. But he may want you to speed up instead, or stop stimulation completely. Once he’s cum, always swallow, and then slowly remove your fingers from inside him. Clean up, and then follow up. Ask him what his favorite part was. If there’s anything else he wants to try next time. And cuddle him!
Let me know if there’s anything I missed, and until next time! :)
Source: reddit.com/r/eroticliterature/comments/z34no1/advanced_blowjob_howto_mf_oral_rimming_anal